Efficient synthesis and reactions of 1,2-dipyrrolylethynes
Various dipyrroles possess important motifs for construction of pyrrole-containing pigments. A series of 1,2-dipyrrolylethynes (4ad) has been efficiently synthesized using an improved one-pot double Sonagashira coupling from trimethylsilylethyne and various 2-iodopyrroles. The resulting 1,2-dipyrrolylethynes were further transformed into novel indolyl-, ethenyl- and carboranyl-dipyrroles (57) using the Larock indole synthesis, stereoselective catalytic hydrogenation, or B10H14. Indolyl-dipyrroles were found to selectively bind fluoride ions using one pyrrolic and the indolyl NHs, whereas the carboranyl- and ethenyl-dipyrroles are potentially valuable precursors for the synthesis of porphyrin isomers and expanded pigments. © 2011 World Scientific Publishing Company.
Publication Source (Journal or Book title)
Journal of Porphyrins and Phthalocyanines
Tanui, H., Hao, E., Ihachi, M., Fronczek, F., Smith, K., & Vicente, M. (2011). Efficient synthesis and reactions of 1,2-dipyrrolylethynes. Journal of Porphyrins and Phthalocyanines, 15 (5-6), 412-420. https://doi.org/10.1142/S1088424611003331